WO1997046097A1 - Novel agricultural/horticultural bactericidal compositions - Google Patents

Abstract

Agricultural/horticultural bactericidal compositions containing as the active ingredients benzamidoxime compounds represented by general formula (I) and so-called acrylate bactericides wherein R1 represents alkyl, alkenyl, etc.; R2 represents phenyl, a heterocycle, etc.; X1 represents haloalkyl; X?2, X3, X4 and X5¿ represent each hydrogen, halogeno, alkyl, etc.; and r¿1? and r2 represent each hydrogen, halogeno, alkyl, etc. These compositions are mixed bactericidal compositions capable of improving the effective control value in a small dose of each active substance.

Description

 Specification

 New agricultural and horticultural fungicide compositions

 The present invention relates to a fungicide composition, particularly a fungicide composition suitable for controlling powdery mildew on various agricultural and horticultural crops. Background technology:

 Equation (I)

で表されるベンジァ ミ ドキシム誘導体は、 本出願人らによ って、 WO 9 6 / 1 9 4 4 2号公報に開示されている殺菌活性を有する化合物である。

Is a compound having a bactericidal activity disclosed by the present applicant in WO96 / 19442.

 In addition, so-called acrylate fungicides represented by ICIA 554, BASF 490, SSF-126, etc. are also known as a new type of agricultural and horticultural fungicide (EP 4 7 7 6 3 1, EP 2 5 3 2 1 3, EP 3 8 3 7 7 etc.).

 However, a fungicide composition containing the compound represented by the formula (I) and a so-called acrylic acid-based fungicide and exhibiting a synergistic effect has not yet been known. DISCLOSURE OF THE INVENTION:

An object of the present invention is to reduce the required amount of these known compounds and to improve the effective spectrum, the amount of each active substance used is small, and the effective control effect can be improved. An object of the present invention is to provide a mixed fungicide composition exhibiting a synergistic effect. The fungicidal composition of the present invention has the following formula (I) as an active ingredient:

(In the formula, R ¹ represents an optionally substituted C, -C alkyl group, an optionally substituted C 2 -C 4 alkenyl group or an optionally substituted C 2 -C alkynyl group, and R ² represents A phenyl group which may have a substituent or a hetero ring which may have a substituent;

X ¹ represents a C, -C ₄ haloalkyl group,

^{X, X '1, X 1} , X 5 , independently of one another, a hydrogen atom, a halogen atom, C, - c, an alkyl group, one C ₄ haloalkyl group, C, - C alkoxy, C, - C Bruno , Mouth alkoxy group, C, -C., Alkylthio group, Ci-C, alkylsulfinyl group, CI-C4 alkylsulfonyl group, nitro group, amino group or c, -c, alkylcarbonyl Represents an amino group,

r,, r ₂ each independently represent a hydrogen atom, a halogen atom, a C, -C „alkyl group, a C, -C 4 haloalkyl group, a C i -C ₄ alkoxy group, a C, -C alkylthio group Or represents an amino group, and I-,, and r may be taken together to form a carbonyl group.]

A fungicidal composition comprising, as active ingredients, a benzamide oxime compound A represented by the following formula (I) and one or more compounds selected from the compound group B shown below.

 (a) (b)

:

 (c) (d)

0CH ₂ C

(i) (J)

(k)

本発明に使用されるべンズア ミ ドキシム化合物は、 前記一般式 （ I ) で表され る化合物であり、 それらの 1種または 2種以上を用いること もできる。

The benzamidoxime compound used in the present invention is a compound represented by the above general formula (I), and one or more of them can be used.

 Preferred specific examples of the benzamide oxime compound represented by the general formula [I] are shown in Table 1.

 Table 1

No. X ₄ R ₂

CH _; Ph

CI CH _; Ph

CI Ph

CI CI CH: Ph

OAVdT3d i / 6-

0 \

 The acrylic acid bactericide referred to in the present invention is a bactericidal substance developed by using a natural compound such as Oudemansin A or Strobi 1 urine A as a sulfide compound. Refers to a substance having an alkoxymethylene group or an alkoxyamino group as a partial structure.

 Preferred examples of the acrylic acid-based bactericides according to the present invention include the compounds shown in the above (a) to (n). Acrylic acid fungicides can exist in an E- or Z-configuration (with respect to carboxylic acid function) due to their C = X double bond. For this purpose, the mixtures according to the invention can be used either pure E-isomer or pure Z-isomer alone or as a mixture of EZZ-both isomers.

 In the fungicidal composition of the present invention, the mixing ratio of the compound A represented by the formula [I] and the acrylic acid-based compound B can be varied over a wide range, but usually, the weight ratio is 1: 1. 0.01 to 100, preferably in the range of 1:] to 100.

 The bactericide composition of the present invention is usually mixed with a solid carrier, a liquid carrier, a gaseous carrier, and the like, and if necessary, added with a surfactant, other formulation auxiliaries, and the like, to prepare an oil, emulsion, water, or the like. It is used as a formulation in Japanese preparations, granules, powders, aerosols, suspensions, foams, microcapsules, ULV preparations, pastes and the like. These preparations usually contain the active ingredient compound in a total amount of 0.1 to 99.9% by weight, preferably 0.2 to 80% by weight.

Examples of the solid carrier used in the formulation include clays (kaolinite, diatomaceous earth, synthetic hydrous silicon oxide, fubasamikura, bentonite, acid clay, etc.), silver, and other inorganic materials. Minerals (cericite, quartz powder, sulfur powder, activated carbon, calcium carbonate Liquid carriers include, for example, water, alcohols (such as methanol and ethanol), and ketones (aceton, methylethylketone, and cyclohexane). Hexane, etc.), aromatic hydrocarbons (toluene, xylene, ethylbenzene, methyl naphthalene, etc.), non-aromatic hydrocarbons (hexane, cyclohexane, kerosene, etc.), esters (acetic acid) , Ethyl acetate, butyl acetate, etc.), nitriles (acetitol nitrile, isoptyronitrile, etc.), ethers (dioxane, diisopropyl ether, etc.), acid amides (dimethylforma). Methane, dimethyl acetate), halogenated hydrocarbons (dichloroethane, trichloroethylene) and the like. As an agent, for example carbon dioxide, pigs Ngasu, and the like Furuorokabon.

 Examples of the surfactant include alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers and their polyoxyethylenates, polyethylene glycol ethers, and polyhydric alcohol esters. Ters, sugar alcohol derivatives and the like. Other pharmaceutical adjuvants include, for example, casein, gelatin, polysaccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonites, synthetic water-soluble polymers (polyvinyl alcohol) Adhesives and dispersants such as styrene, polyvinylpyrrolidone, polyacrylic acid, etc., PAP (isopropyl oxyphosphate), BHT (2,6-diethyl butyl 4- 4-methyl phenol) ), Stabilizers such as BHA (2- / 3-tert-butyl-4- 4-methoxyphenol), vegetable oils, mineral oils, fatty acids and fatty acid esters. The formulated fungicide composition of the present invention is applied to a plant, water surface or soil as it is or after dilution with water or the like. It can also be used in combination with other fungicides, insecticides, herbicides, fertilizers, soil conditioners, and the like. The application rate of the fungicide composition of the present invention depends on the mixing ratio of the compound represented by the formula (I), which is the active ingredient compound, and the so-called acrylate fungicide, weather conditions, formulation, application time, and application method. Although it varies depending on the application site, the disease to be controlled, the target crop, etc., the amount of the active ingredient compound is usually 1 per hectare.

~ 100 g, preferably 100-100 g. When the emulsions, wettable powders, suspensions, liquids, etc. are applied after dilution with water, the application concentration is from 1 to 100 ppm, preferably from 10 to 250 pm. Agents, powders, etc. are usually applied without dilution To use.

 BEST MODE FOR CARRYING OUT THE INVENTION

 (Example)

 Hereinafter, Test Examples show that the compound of the present invention is useful as a powdery mildew control agent for various agricultural and horticultural crops. The control effect was determined by visually observing the degree of disease spots that appeared on the leaves at the time of the survey, and comparing it with the untreated one. The simple emulsion was prepared by mixing the compound A represented by the general formula (I) (Compound No. 1 in Table 1) and the acrylic acid fungicide B (1) at a predetermined ratio. did.

Test example 1 Wheat powdery mildew control test

 Wheat seedlings (variety “Chihoku” 1-1.5 leaf stage) cultivated in unglazed pots were sprayed with a simple emulsion of the mixture of the present invention at a predetermined concentration. After air-drying at room temperature, conidia of wheat spores (Ery sip h e g ram a m ni s f. S p. The appearance of disease spots on the leaves was compared with the untreated plot, and the control effect was determined. Table 2 shows the results.

 The expected effectiveness E of the present invention was calculated from Colby's formula (Weed., 15.20-22, 1966.6), and the observation results were compared.

 · Y

 E = X + y—

 1 0 0

E shows the expected efficacy in% when active substances A and B are used at concentrations m and n, and X shows the efficacy in% when active substance A is used at concentration m. And y indicate the effectiveness in% when the active substance B is used at a concentration of n. Table 2 Effective substances Concentration of active substances in the spray liquid Actual effectiveness Calculation effectiveness

 (P p m) (%) (%) Water (untreated) 0 0

2 1 3 to W096 / 19442

 Described compound A 0 5 0

 (No.1) Known substance B 0 0 5 3 8

 (1) 0 0 1 2 5 1 9

A + B 0.2 + 0.05 8 1 4 1

 0.2 + 0. 0 1 2 5 7 5 3 0

 0.05 + 0.0 5 5 9 3 8

These experimental results show that the actual effectiveness is improved over the effectiveness calculated from Colby's equation.

Industrial applicability:

 As described above, the present invention provides a fungicidal composition that is extremely effective in controlling various agricultural and horticultural crop diseases, in particular, various powdery mildews.

Claims

The scope of the claims  1. Formula [I]

[In the formula, R ¹ is an optionally substituted C, -C 4 alkyl group, an optionally substituted C 2-c, an alkenyl group or an optionally substituted c ₂ -C ₄ alkynyl group, R ² represents a phenyl group which may have a substituent or a hetero ring which may have a substituent, X ¹ represents a C, —C ₄ haloalkyl group, X ² , X ³ , X ⁴ , and X ⁵ are each independently a hydrogen atom, a halogen atom, a C, -C 4 alkyl group, a C, -C 4 haloalkyl group, a C, -C, an alkoxy group, a C, - C ₄ haloalkoxy group, - C 4 alkylthio group, C, - C, alkylsulfinyl Fi group, c] - C 4 alkylsulfonyl group, a nitro group, A Mi amino group or C, - C, alkylcarbonyl § Represents a amino group, r,, r ₂ are each independently a hydrogen atom, a halogen atom, C, - C _t Al kill groups, - C -, haloalkyl groups, C, - C ₄ alkoxy groups, C, - C Al Kiruchio group or Represents an amino group, and r 1, and r 2 may be taken together to form a carbonyl group. ] And a fungicide comprising, as active ingredients, one or more compounds selected from the group consisting of the compounds (a) to (n) shown below. Composition.

(k)